My Pretty Bo Peep


My favorite ladyboy had been a very good girl that week before the play party. She invited Me over for an evening of pampering. She put on her prettiest maid’s outfit, bathed Me and made sure I was properly smooth, cooked Me a wonderful dinner, brought Me drinks, listened as I spoke without interrupting even once, and serviced Me well before My sleep. She also made a point of beginning every day by phoning to tell Me how devoted she was.


Being the loving Mistress that I am, I thought back to a conversation we'd had the previous month about a fantasy she had not yet fulfilled: she had confessed that she longed to be forced against her will to wear a pretty, über-feminine dress in public. Given her recent excellent conduct, I decided to execute her fantasy on Saturday night, when we would be attending our city's largest monthly play party. This particular gathering typically draws a crowd of 150–300 people, making it the perfect venue for My purposes, as I know how much she enjoys showing herself off! And I certainly had a show in mind.


Since sissies simply love surprises, I didn't utter a peep about the special treat in store for her at Saturday's gala. That evening, she showed up at the party dressed more boyishly than is her wont, which just played into My hands all the more. After the party had been underway for a while and a T-cross became available, I began laying out My things. She was curious as to My plan, for we had not discussed the scene beforehand, nor had I indicated that she would be watching while I did a demo with another sub. I said nothing, continuing to set up the space.


Eventually, I called her over to Me and told her to remove her shoes, shirt, and pants, which she willingly did. I then put leather restraints on her wrists and ankles. I showed her the contents of My bag: a very frilly blue-and-white Bo Peep outfit, complete with cap and apron, with a separate petticoat, frilly white panties, white thigh-high stockings, and her shiniest Mary Janes.


She positively howled in protest, saying there was no way that she was going to put on such a "girly" outfit. And furthermore, I could not make her.


Of course, she knew full well that I would not tolerate such insolence from her. And in any case, I could already see a wet spot forming on the front of her panties. But her tantrum had drawn the attention of other guests, and I could hardly let her get away with such a public display of bad manners.


Not that I would in private, either.


I grabbed one of her wrists and dragged her toward the cross. She squirmed and protested, but her slippery socks slid on the smooth floor and made it impossible for her to break loose. I deftly lifted her arm to the cross and slipped the hook into her cuff. She immediately tried to open it, but I picked up My riding crop and smacked her across the ass and thighs repeatedly, telling her to leave that restraint alone. She was so distracted by the blows that it was merely a matter of seconds before the other wrist was within easy distance of the second hook. Snap. Before I could get her ankles restrained, however, she figured out how to unhook herself with one hand! Secretly, I found it amusing, but there were many eyes on us, and I certainly could not allow such outrageous conduct to go uncorrected. I quickly put a spreader bar on her ankle cuffs as she went for the second hook. Her arms were temporarily free, but the spreader bar hampered her escape, and she managed to wriggle only a few feet away before I grabbed her. Taking no chances this time, I secured her leash to her collar, dragged her back to the cross, and lashed the leash around it, immobilizing her head. She put up a good struggle as I rehooked her wrist and ankle cuffs, protesting the entire time that there was no way I could make her wear such a stupid, frilly, girly dress, but in short order I had her back in place.


I had to punish her for disobeying Me. I pulled her panties down to her knees so that she was completely on display for everyone to see. Her insolent attitude continued unabated, even as her precum dangled from between her thighs. I picked up My rubber whip—one of My favorites due to the sharpness of the strike and the marks that it leaves—and began flicking it at her pretty ass. She struggled valiantly, but with her leash tied firmly to the cross, she couldn’t see to get her wrists free again. Very soon, she was apologizing loudly for all to hear: Oh, how sorry she was for having disobeyed Mistress! I left her with a very sore, red ass for her troubles.


While her eyes were closed and she was recovering her breath, I unhooked one ankle cuff at a time so I could remove her everyday panties and put on the very frilly white ones. I put her in the fluffy petticoat and rehooked her cuffs. I then pulled her panties and petticoat up to her waist. At this point, she opened her eyes, but unfortunately, she also opened her mouth—and had the audacity to argue with Me, yet again! Some pinches to her already tender ass fixed that attitude problem in no time flat. 


In that manner, I completed her toilette—put one piece on, get attitude, smack her sweet ass and remind her that she has no choice but to do as I wish, get apology—and so the cycle continued. Finally I had her completely dressed from head to toe.


I began telling her how very pretty and feminine she looked, but as a last act of defiance, she refused to open her eyes and look for herself. I took hold of her hair and brought her lips to Mine, and she happily returned My kiss. I reached up under her petticoat and stroked her panties against her once, very gently. She moaned into My mouth. I told her to open her eyes and see what a pretty girl she had become. She did so, audibly gasping at the look of the dress on her, the heavy frills of the petticoat, the big bows, the little girl shoes. She seemed very happy, fulfilled even, as she looked down at herself. I removed her wrist and ankle cuffs but left her leash on. I instructed her to twirl and feel the petticoat swirling around her thighs, and twirl she did, like a top. I then paraded her around the room, showing off her beauty. She received many compliments, and each one made her glow that much more.


But I wasn’t done with her yet.


I continued promenading her around until we reached the bathroom. I wanted her to look at herself in a mirror, and a big one at that. As soon as she saw her reflection, she became shy and a bit belligerent again. I grabbed her leash and dragged her closer to the mirror. I told her to bend over and rest her hands on the counter while examining herself. I had had just about enough of her impertinent attitude for one night, and My tone of voice was such that this time, she obeyed Me without a struggle.


I pulled her frilly panties down and commanded her to say, “I look pretty.” When she did not immediately comply, I smacked that tender ass of hers. She jumped and mouthed the words, but she was mumbling and looking away. I smacked her again, eliciting a better performance, but still too quiet. I continued to spank her ass hard until she said the line correctly, as if she believed it, as if she was proud of it, and loudly enough for the people outside to hear. I then pulled her new frilly panties up, took her in My arms, and told her that she was pretty, and it pleased Me so to see her looking beautiful, because her beauty redounded to My credit. She hugged Me tightly and thanked Me.


For the rest of the evening, she modeled a succession of different outfits at My whim, never looking happier. And every time someone brings up that evening in conversation, she still smiles.


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